I won't comment on your potential choices as I have no experience with them, other than when growing up with a D17 that a neighbor had as his primary tractor, this when it was nearly new however (fine tractor, very smooth running and strong).
My experience was similar to yours, had some acreage, needed a tractor to do some mowing and dirt and snow moving. I got a 9N from the guy that built my house and it served me well for many years, this was about 25 yrs ago. I bought an 8N at a sale about 13 yrs. ago because when the 9N was down I was done and I had pastures to mow and manure to spread at a new place. At least I'd have a backup while the other one was worked on. For small acreage I never felt I didn't have enough power to do what I had to do, it just happened slower than with bigger tractors. My thinking was exactly where yours is (at least when you wrote the post) but after looking around was uneasy about potentially buying someone's problems. So last year I bought my first new tractor, I was joining the ranks of senior citizens and wanted a FEL and something that was very reliable to help with things around the place (and the car was finally paid off!). I stayed small (22 hp) in order to move in and out of the barn and yet do mowing and lifting. So I got what I needed and no more. My experience and my planned usage said the Mahindra eMax 22 was plenty of tractor and in the budget , even the wife agreed due to the price and financing, 5 yr. warranty and all the things I promised we could now do. But that's me...
We tend on this forum to gleefully spend other peoples money for the bigger and fancier tractors. If this thread grows we'll insist that you need a 40 - 50 hp tractor, maybe with a cab, grapple on the FEL, full complement of front and rear hydraulic outlets, oh, yea, A/C for that cab, maybe a snow thrower/blower, front mount of course. Nothing but a Kubota/New Holland/Kioti/LS/Case IH/Mahindra/Massey/you name it will do. In the end only you know what you can spend and how you can handle maintenance and repairs... some good advice already given on that aspect. If you can see clear to afford something a bit newer and more compatible for FEL use I'd give that some serious thought, although maybe you would be excited about replacing broken or bent spindles or an axle pivot pin. If you really aren't sure, start out with a very reasonable price Ford N, Ford 100 series or Massey 35, a used "bush hog" mower and a back blade, maybe a 3pt scoop and have at it. You'll soon learn what you want and need and can make the best decision for you when you get ready to move up, if you want to at all. Good luck.